EP1742998A1 - Polyarylene ether compression molding - Google Patents
Polyarylene ether compression moldingInfo
- Publication number
- EP1742998A1 EP1742998A1 EP05735268A EP05735268A EP1742998A1 EP 1742998 A1 EP1742998 A1 EP 1742998A1 EP 05735268 A EP05735268 A EP 05735268A EP 05735268 A EP05735268 A EP 05735268A EP 1742998 A1 EP1742998 A1 EP 1742998A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- powder
- poly
- arylene ether
- binder
- pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 142
- 238000000748 compression moulding Methods 0.000 title claims abstract description 16
- 229920000412 polyarylene Polymers 0.000 title abstract 5
- 239000000843 powder Substances 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 55
- 230000006835 compression Effects 0.000 claims abstract description 51
- 238000007906 compression Methods 0.000 claims abstract description 51
- 238000005056 compaction Methods 0.000 claims abstract description 22
- 230000009477 glass transition Effects 0.000 claims abstract description 9
- -1 poly(arylene ether Chemical compound 0.000 claims description 139
- 239000011230 binding agent Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 29
- 239000002245 particle Substances 0.000 claims description 22
- 239000003063 flame retardant Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 238000001125 extrusion Methods 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000004604 Blowing Agent Substances 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000006082 mold release agent Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- 239000008188 pellet Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 14
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920000359 diblock copolymer Polymers 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000005691 oxidative coupling reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 229920000428 triblock copolymer Polymers 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- FGHOOJSIEHYJFQ-UHFFFAOYSA-N (2,4-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=C(OP(O)O)C(C(C)(C)C)=C1 FGHOOJSIEHYJFQ-UHFFFAOYSA-N 0.000 description 1
- FJUJZGNQVISAPS-UHFFFAOYSA-N (4-methylphenyl) bis(2,5,5-trimethylhexyl) phosphate Chemical compound CC(C)(C)CCC(C)COP(=O)(OCC(C)CCC(C)(C)C)OC1=CC=C(C)C=C1 FJUJZGNQVISAPS-UHFFFAOYSA-N 0.000 description 1
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- UHFOGRFLWQICFT-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-1,1-diphenylpropane-1,3-diol phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(=O)(O)O.C1(=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=CC=CC=C1 UHFOGRFLWQICFT-UHFFFAOYSA-N 0.000 description 1
- JSOGDEOQBIUNTR-UHFFFAOYSA-N 2-(azidomethyl)oxirane Chemical compound [N-]=[N+]=NCC1CO1 JSOGDEOQBIUNTR-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- ROHFBIREHKPELA-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O ROHFBIREHKPELA-UHFFFAOYSA-N 0.000 description 1
- NCVFZIASVZHSOI-UHFFFAOYSA-N 2-chloroethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCl)OC1=CC=CC=C1 NCVFZIASVZHSOI-UHFFFAOYSA-N 0.000 description 1
- QDLYDXLYPXBEKO-UHFFFAOYSA-N 2-ethylhexyl bis(4-methylphenyl) phosphate Chemical compound C=1C=C(C)C=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=C(C)C=C1 QDLYDXLYPXBEKO-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- OBTARUYASFQRHM-UHFFFAOYSA-N benzene-1,3-diol;diphenoxyphosphoryl diphenyl phosphate Chemical compound OC1=CC=CC(O)=C1.C=1C=CC=CC=1OP(OP(=O)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 OBTARUYASFQRHM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OFOXPUGNNSFGPE-UHFFFAOYSA-N bis(2,2-dimethylpropyl) phenyl phosphate Chemical compound CC(C)(C)COP(=O)(OCC(C)(C)C)OC1=CC=CC=C1 OFOXPUGNNSFGPE-UHFFFAOYSA-N 0.000 description 1
- XIMUORXKUCOUFY-UHFFFAOYSA-N bis(2-ethylhexyl) (4-methylphenyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OC1=CC=C(C)C=C1 XIMUORXKUCOUFY-UHFFFAOYSA-N 0.000 description 1
- ZXZYMQCBRZBVIC-UHFFFAOYSA-N bis(2-ethylhexyl) phenyl phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 ZXZYMQCBRZBVIC-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- PWFPXTOTJCXQEM-UHFFFAOYSA-N butanedioic acid;2-[2-(2-hydroxyethoxy)ethoxy]ethanol Chemical compound OC(=O)CCC(O)=O.OCCOCCOCCO PWFPXTOTJCXQEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 description 1
- RYSCVIAVOSESIU-UHFFFAOYSA-N didodecyl (4-methylphenyl) phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OC1=CC=C(C)C=C1 RYSCVIAVOSESIU-UHFFFAOYSA-N 0.000 description 1
- OHZIKCOBQFCTDM-UHFFFAOYSA-N didodecyl phenyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OC1=CC=CC=C1 OHZIKCOBQFCTDM-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JSPBAVGTJNAVBJ-UHFFFAOYSA-N ethyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCC)OC1=CC=CC=C1 JSPBAVGTJNAVBJ-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 235000021189 garnishes Nutrition 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- GHHZPPRXDWBHQA-UHFFFAOYSA-N phenyl bis(3,5,5-trimethylhexyl) phosphate Chemical compound CC(C)(C)CC(C)CCOP(=O)(OCCC(C)CC(C)(C)C)OC1=CC=CC=C1 GHHZPPRXDWBHQA-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012758 reinforcing additive Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C43/00—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C43/00—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor
- B29C43/003—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor characterised by the choice of material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C43/00—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor
- B29C43/006—Pressing and sintering powders, granules or fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C43/00—Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor
- B29C43/32—Component parts, details or accessories; Auxiliary operations
- B29C43/52—Heating or cooling
- B29C2043/522—Heating or cooling selectively heating a part of the mould to achieve partial heating, differential heating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2071/00—Use of polyethers, e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2071/00—Use of polyethers, e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof, as moulding material
- B29K2071/12—PPO, i.e. polyphenylene oxide; PPE, i.e. polyphenylene ether
Definitions
- This disclosure relates to poly(arylene ether) and more particularly to methods of forming articles from poly(arylene ether).
- Poly(arylene ether) resins are commercially attractive materials because of their unique combination of physical, chemical, and electrical properties. They are a widely used class of thermoplastic engineering resins characterized by excellent hydrolytic stability, dimensional stability, toughness, heat resistance, and dielectric properties. Furthermore, the combination of poly(arylene ether) with other resins provides blends that result in additional overall desirable properties such as chemical resistance, high strength, and high flow.
- Poly(arylene ether) is commercially available blended with other resins such as poly(styrene), polypropylene and polyamide. These blends are usually made using poly(arylene ether) powder.
- the poly(arylene ether) powder that is used in the preparation of polymer blends may have a wide particle size distribution, which can affect processability.
- the density of the poly(arylene ether) powder is generally less than or equal to 0.6 gram per cubic centimeter. Such a low density requires large volumes for storage and transportation.
- due to the fluffy nature of the poly(arylene ether) powder it is difficult to feed to an extruder at higher feed rates.
- the method comprises introducing a powder comprising unheated poly(arylene ether) powder to compaction equipment comprising a compression mold and subjecting the powder in the compression mold to a pressure sufficient to produce an article having a density greater than the unheated poly(arylene ether) powder wherein the pressure is applied at a temperature less than the glass transition temperature of the poly(arylene ether) powder.
- a method for compression molding poly(arylene ether) powder comprises introducing an unheated poly(arylene ether) powder to compaction equipment comprising a compression mold, and applying sufficient pressure to the powder in the compression mold to produce an article.
- poly(arylene ether) powder refers to a powder consisting essentially of poly(arylene ether) resin or a combination of two or more poly(arylene ether) resins.
- the compression molding method may be performed by batch or continuous processing.
- Poly(arylene ether)s are known polymers comprising a plurality of structural units of the formula (I):
- each Q is independently hydrogen, halogen, primary or secondary lower alkyl (e.g., alkyl containing up to 7 carbon atoms), phenyl, haloalkyl, aminoalkyl, hydrocarbonoxy, halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each Q 2 is independently hydrogen, halogen, primary or secondary lower alkyl, phenyl, haloalkyl, hydrocarbonoxy, halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms.
- each Q 1 is alkyl or phenyl, especially C alkyl
- each Q 2 is hydrogen.
- Both homopolymer and copolymer poly(arylene ether)s may be included.
- Exemplary homopolymers include those containing 2,6-dimethyl-l,4-phenylene ether units.
- Suitable copolymers include random copolymers containing such units in combination with (for example) 2,3,6-trimethyl-l,4-phenylene ether units.
- poly(arylene ether)s containing moieties prepared by grafting vinyl monomers or polymers such as polystyrenes and elastomers, as well as coupled poly(arylene ether)s in which coupling agents such as low molecular weight polycarbonates, quinones, heterocycles and f ⁇ rmals undergo reaction in a known manner with the hydroxy groups of two poly(arylene ether) chains to produce a higher molecular weight polymer.
- Poly(arylene ether)s further include combinations of any of the above.
- the poly(arylene ether) generally has a number average molecular weight of about 3,000- 40,000 atomic mass units (amu) and a weight average molecular weight of about 20,000- 80,000 amu, as determined by gel permeation chromatography.
- the poly(arylene ether) may have an intrinsic viscosity of about 0.08 to about 0.60 deciliters per gram (dl/g), or, more specifically, about 0.29 to about 0.48 dl/g, as measured in chloroform at 25°C It is also possible to utilize a high intrinsic viscosity poly(arylene ether) and a low intrinsic viscosity poly(arylene ether) in combination. Determining an exact ratio, when two intrinsic viscosities are used, will depend somewhat on the exact intrinsic viscosities of the poly(arylene ether) used and the ultimate physical properties that are desired.
- Poly(arylene ether) is generally prepared by the oxidative coupling of at least one monohydroxyaromatic compound such as 2,6-xylenol or 2,3,6-trimethylphenol.
- Catalyst systems are generally employed for such coupling; they generally contain at least one heavy metal compound such as a copper, manganese or cobalt compound, usually in combination with various other materials.
- Particularly useful poly(arylene ether) for many purposes are those which comprise molecules having at least one aminoalkyl-containing end group.
- the aminoalkyl radical is generally located in an ortho position to the hydroxy group.
- Products containing such end groups may be obtained by incorporating an appropriate primary or secondary monoamine such as di-n-butylamine or dimethylamine as one of the constituents of the oxidative coupling reaction mixture.
- 4-hydroxybiphenyl end groups generally obtained from reaction mixtures in which a by-product diphenoquinone is present, especially in a copper-halide-secondary or tertiary amine system.
- a substantial proportion of the polymer molecules typically constituting as much as about 90% by weight of the polymer, may contain at least one of said aminoalkyl-containing and 4-hydroxybiphenyl end groups.
- the poly(arylene ether) may be functionalized with a functionalizing agent comprising (a) at least one carbon-carbon double bond or carbon-carbon triple bond and (b) at least one functional group selected from carboxylic acid, acid anhydride, acid amide, imide, ester, amino, hydroxy, and the like.
- the functionalizing agent comprises maleic anhydride.
- Other functionalizing agents, as well as functionalizing methods, are described, for example, in U.S. Patent No. 4,888,397 to van der Meer et al., and Japanese Patent Publication No. 2003-183385 to Tokiwa et al.
- poly(arylene ether)s include many of those presently known, irrespective of variations in structural units or ancillary chemical features.
- the poly(arylene ether) is in powder form and may have an average particle size of about 50 micrometer to about 1500 micrometers, or, more specifically about 75 micrometers to about 1250 micrometers, or, even more specifically, about 90 micrometers to about 1000 micrometers.
- the poly(arylene ether) powder has a wide particle size distribution, ranging in size from about 0.2 micrometers to about 5,000 micrometers.
- Particles, as used herein, may be individual particles or individual particles associated together as agglomerates and/or aggregates.
- the poly(arylene ether) powder comprises about 5 to about 70, or, more specifically, about 10 to about 65, or, even more specifically about 15 to about 60 volume percent of particles having a particle size less than about 100 micrometers, based on the total volume of the poly(arylene ether).
- having a combination of particle sizes allows the smaller particles to pack between the larger particles and form an article having greater compressive strength.
- the density of the poly(arylene ether) powder is less than or equal to about 0.6 grams per cubic centimetre(g/cm 3 ), or more specifically, about 0.2 to about 0.5 g/cm 3 , or, even more specifically about 0.4 to about 0.5 g/cm .
- the poly(arylene ether) powder may optionally comprise various additives, for example, anti-oxidants, flame retardants, mold release agents, ultraviolet absorbers, stabilizers such as light stabilizers and others, lubricants, plasticizers, pigments, dyes, colorants, antistatic agents, blowing agents, and mixtures thereof.
- additives for example, anti-oxidants, flame retardants, mold release agents, ultraviolet absorbers, stabilizers such as light stabilizers and others, lubricants, plasticizers, pigments, dyes, colorants, antistatic agents, blowing agents, and mixtures thereof.
- antioxidants include organophosphites, for example, tris(nonyl-phenyl) phosphite, tris(2,4-di-t- butylphenyl)phosphite, bis(2,4-di-t-butylphenyl) pentaerythritol diphosphite, 2,4-di-tert- butylphenyl phosphite, or distearyl pentaerythritol diphosphite, alkylated monophenols, polyphenols and alkylated reaction products of polyphenols with dienes, such as, for example, tetrakis [methylene(3,5-di-tert-butyl-4-hydroxyhydrocinnamate)] methane and 3,5-di-tert-butyl-4-hydroxyhydrocinnamate octadecyl; butylated reaction products of para-cresol and dicyclopentadiene; alkylated reaction
- Fillers and reinforcing agents may also be used, such as, for example, silicates, titanium dioxide, fibers, glass fibers (including continuous and chopped fibers), carbon black, graphite, calcium carbonate, talc, and mica.
- silicates titanium dioxide
- fibers fibers
- glass fibers including continuous and chopped fibers
- carbon black graphite
- calcium carbonate calcium carbonate
- talc talc
- mica mica
- Suitable flame retardants may be organic compounds that include phosphorus, bromine, and/or chlorine.
- Non-brominated and non-chlorinated phosphorus-containing flame retardants may be preferred in certain applications for regulatory reasons, for example organic phosphates and organic compounds containing phosphorus-nitrogen bonds.
- Two of the G groups may be joined together to provide a cyclic group, for example, diphenyl pentaerythritol diphosphate, which is described by Axelrod in U.S. Pat. No. 4,154,775.
- aromatic phosphates may be, for example, phenyl bis(dodecyl) phosphate, phenyl bis(neopentyl) phosphate, phenyl bis(3,5,5'-trimethylhexyl) phosphate, ethyl diphenyl phosphate, 2-ethylhexyl di(p-tolyl) phosphate, bis(2-ethylhexyl) p-tolyl phosphate, tritolyl phosphate, bis(2-ethylhexyl) phenyl phosphate, tri(nonylphenyl) phosphate, bis(dodecyl) p-tolyl phosphate, dibutyl phenyl phosphate, 2-chloroethyl diphenyl phosphate, p-tolyl bis(2,5,5'-trimethylhexyl) phosphate, 2-ethylhexyl diphenyl phosphate,
- Di- or polyfunctional aromatic phosphorus-containing compounds are also useful, for example, compounds of the formulas below:
- suitable di- or polyfunctional aromatic phosphorus-containing compounds include resorcinol tetraphenyl diphosphate (RDP), the bis(diphenyl) phosphate of hydroquinone and the bis(diphenyl) phosphate of bisphenol-A (, respectively, their oligomeric and polymeric counterparts, and the like. Methods for the preparation of the aforementioned di- or polyfunctional aromatic compounds are described in British Patent No. 2,043,083.
- the mixture may comprises about 1 to about 40 weight percent flame retardant, or, more specifically, about 1 to about 30 weight percent, or, even more specifically, about 1 to about 20 weight percent flame retardant, based on the total weight of the mixture.
- a binder may be added to the poly(arylene ether) to form a mixture having improved cohesion between the particles of the poly(arylene ether) powder.
- the binder provides flexibility in manufacturing articles using the compression molding method.
- the binder does not cause irreversible agglomeration of the particles of poly(arylene ether) powder when combined with the poly(arylene ether) powder prior to molding.
- the mixture may comprise about 60 about 99.99 weight percent poly(arylene ether) powder, or, more specifically about 90 to about 99.9 weight percent, or, even more specifically, about 95 to about 99.5 weight percent, based on the total weight of the mixture.
- the mixture may comprise about 0.01 to about 40 weight percent binder, or, more specifically about 0.1 to about 10 weight percent, or, even more specifically, about 0.5 to about 5 weight percent binder based on the total weight of the mixture.
- the binder may be a reactive binder, non-reactive binder or a combination thereof.
- the binder when polymeric or oligomeric, may be crystalline or amorphous. When the binder is crystalline, the binder has a melt temperature less than or equal to the glass transition temperature (Tg) of the poly(arylene ether). When the binder is amo ⁇ hous, the binder has a Tg less than or equal to the poly(arylene ether) Tg.
- a non-reactive binder may be any polymer or oligomer that is non-reactive with the poly(arylene ether) powder and itself.
- Useful non-reactive binders include vinyl acetate and its derivatives including vinyl acetate oligomers and polymers, oligomers of ethylene vinyl acetate , high impact polystyrenes (HIPS), polyolefins, and polytetrafluoroethylene dispersed in a styrene-acrylonitrile copolymer.
- the polytetrafluoroethylene is usually present in the dispersion in an amount of about 40 to about 60 weight percent based on the total weight of the dispersion.
- Non-reactive binders include elastomeric block copolymers, for example, A- B-A triblock copolymers and A-B diblock copolymers.
- elastomeric block copolymers for example, A- B-A triblock copolymers and A-B diblock copolymers.
- Suitable A-B and A-B-A type block copolymers are disclosed in, for example, U.S. Patent Numbers 3,078,254, 3,402,159, 3,297,793, 3,265,765, and 3,594,452 and U.K. Patent 1,264,741.
- the elastomeric block copolymer comprises polystyrene-poly(ethylene- butylene)-polystyrene(SEBS), polystyrene-polybutadiene-polystyrene(SBS), polystyrene- poly(ethylene-propylene) (SEP) copolymers or a combination of two or more of the foregoing elastomeric block copolymers.
- SEBS polystyrene-poly(ethylene- butylene)-polystyrene
- SBS polystyrene-polybutadiene-polystyrene
- SEP polystyrene- poly(ethylene-propylene) copolymers or a combination of two or more of the foregoing elastomeric block copolymers.
- a reactive binder may be either self reactive or reactive with the poly(arylene ether) powder. The presence of a binder may improve the appearance of the compressed poly(arylene
- Useful reactive binders include functionalized oligomers wherein the functional group is selected from the group consisting of carboxyl, acyloxy, imino, imido, hydroxy, glycidyl, amine and epoxy.
- Exemplary reactive binders include, but are not limited to, hydroxy terminated polybutadiene, epoxidized polybutadiene, epoxidized vegetable oils, amine terminated polyethylene glycols, poly glycidyl azide oils, hydroxy terminated triethylene glycol succinate polyesters and combinations of two or more of the foregoing reactive binders.
- One or more volatile components may be present in the poly(arylene ether) powder. These volatile components may act as binders when compression molding is carried out at room temperature.
- a modifying agent comprising one or more polar groups may be added to the poly(arylene ether) powder.
- Useful modifying agents include acid halides, carbonyl containing compounds, acid anhydrides, acid amides, carboxylates, acid azides, sulfone containing compounds, nitrile containing compounds, cyano containing compounds, isocyanate esters, amine containing compounds, imide containing compounds, hydroxyl containing compounds, epoxy containing compounds, oxazoline containing compounds, and thiol containing compounds.
- the compression molding method may comprise cold compaction or warm compaction of the poly(arylene ether) powder and may produce a single phase or multi phase compact.
- a multi-phase (or two phase) solid article may comprise a fused cover of the mixture surrounding a core of compressed poly(arylene ether) powder mixture.
- a multi-phase article may comprise a fused binder extending throughout the article. The binder may be grafted or end capped on the poly(arylene ether) powder.
- Compression molding increases the bulk density of the poly(arylene ether) and thereby reduces volume.
- Cold compaction comprises subjecting an unheated poly(arylene ether) powder and optional components to pressure sufficient to form an article having a density of about 0.6 g/cm 3 to about 1.2 g/cm 3 and a compressive strength of about 5 kilograms(kg) to about 3000 kilograms(kg).
- the density may be greater than or equal to about 0.6 g/cm 3 , or, more specifically, greater than or equal to about 0.65 g/cm 3 .
- the density may be less than or equal to about 1.2 g/cm , or, more specifically, less than or equal to about 1.1 g/cm 3 .
- the compressive strength may be.
- the compressive strength may be less than or equal to 3000 kg, or, more specifically, less than or equal to 2500 kg, or, even more specifically, less than or equal to 2000 kg.
- the poly(arylene ether) powder may be blended with the optional components prior to introduction to the compaction equipment, or if the compaction equipment comprises a means for mixing the components the poly(arylen ether) powder and optional components may be added simultaneously or sequentially.
- the applied pressure is about 0.05 tons per square centimetre (tons/cm ) to about 50.0 tons/cm 2 .
- the applied pressure may be greater than or equal to about 1 ton/cm , or, more specifically, greater than or equal to about 2 tons/cm , or, even more specifically, greater than or equal to about 3 tons/cm 2 .
- the applied pressure may be less than or equal to about 20 tons/cm 2 , or, more specifically, less than or equal to about 15 tons/cm 2 , or, even more specifically, less than or equal to about 7 tons/cm 2 .
- ton refers to a metric ton.
- Pressure is applied for about 0.1 seconds to about 100 seconds. Within this range pressure may be applied for greater than or equal to about 2 seconds, or, more specifically, greater than or equal to about 5 seconds. Also within this range, pressure may be applied for less than or equal to about 15 seconds, or, more specifically, less than or equal to about 10 seconds.
- Compression occurs at a temperature less than the Tg of the poly(arylene ether), typically at a temperature of about 0 degrees centigrade (°C) to about 70°C.
- the temperature may be greater than or equal to about 5°C, or, more specifically, greater than or equal to about 10°C, or, even more specifically, greater than or equal to about 15°C.
- the temperature may be less than or equal to about 65°C, or, more specifically, less than or equal to about 60°C, or, even more specifically, less than or equal to about 55° C.
- Warm compaction comprises introducing unheated poly(arylene ether) and optional components to compaction equipment and subjecting the poly(arylene ether) powder and optional components to sufficient pressure and temperature to form an article.
- the compression temperature is less than the Tg of the poly(arylene ether).
- the poly(arylene ether) powder and optional components, once in the compaction equipment, are heated to a temperature sufficient to at least soften the binder, when present, or the poly(arylene ether) and the binder when the binder is present, or the poly(arylene ether) in the absence of a binder to produce an at least softened poly(arylene ether) powder or poly(arylene ether) powder mixture; applying and maintaining sufficient pressure to the at least softened poly(arylene ether) powder or poly(arylene ether) powder mixture while the temperature of the at least softened poly(arylene ether) powder or poly(arylene ether) powder mixture is decreased to form an article having a density of greater than or equal to about 0.95 g/cm 3 and a compressive strength greater than or equal to about 4000 kg.
- the article density may be less than or equal to about 1.2 g/cm 3 .
- the density may be greater than or equal to about 1.0 g/cm 3 , or, more specifically, greater than or equal to about 1.05 g/cm 3 . Within this range the density may be less than or equal to about 1.5 g/cm 3 , or, more specifically, less than or equal to about 1.1 g/cm 3 .
- the compressive strength may be greater than or equal to about 5000 kg, or, more specifically, greater than or equal to about 6000 kg.
- the individual components may be added simultaneously or sequentially to the compaction equipment.
- the poly(arylene ether) powder may be mixed with the optional components, such as a binder, in a dry . blender prior to introducing the mixture to a cavity of a confined pressure device or to the feedthroat of an extruder. Batch or quasi-continuous flow mixing may be used.
- the binder and some or all of the other optional components may be introduced via a first feed port of an extruder and the binder melted or softened by heating the extruder or by virtue of a shearing action of the extruder.
- the poly(arylene ether) powder is added via a second feed port of the extruder and mixed with the molten binder, wherein the second feed port is downstream of the first feed port.
- the compression usually occurs at a temperature greater than the melt temperature of the binder and less than the Tg of the poly(arylene ether) powder, when the binder is crystalline.
- the compression occurs at a temperature greater than the Tg of the binder and less than the Tg of the poly(arylene ether) powder, when the binder is amorphous.
- the pressure applied is about 0.2 tons/cm 2 to about 20 tons/cm 2 . Within this range the pressure applied may be greater than or equal to about 0.25 tons/cm , or, more specifically, greater than or equal to about 0.5 tons/cm 2 or, even more specifically, greater than or equal to about 1.0 tons/cm 2 . Also within this range the pressure applied may be less than or equal to about 10.0 tons/cm 2 , or, more specifically, less than or equal to about 5.0 tons/cm 2 , or, even more specifically, less than or equal to about 2.5 tons/cm 2 . Pressure may be applied for about 300 seconds to about 2000 seconds. Within this range pressure may be applied for greater than or equal to about 500 seconds, or, more specifically, greater than or equal to about 900 seconds. Also within this range, pressure may be applied for less than or equal to about 1500 seconds, or, more specifically, less than or equal to about 1200 seconds.
- the compression method comprises mixing the poly(arylene ether) powder with a solution of the binder in a solvent, and the mixture is isolated by devolatilization of the solvent.
- Suitable binder solutions include solutions resulting from polymerisation of the binder or a process following polymerisation, or the dissolution of the isolated binder in a solvent.
- the term solution includes both solutions and suspensions.
- Devolatization is the removal of solvent through the elevation of temperature, the reduction of pressure or a combination thereof. The devolatization is carried out at a temperature less than the Tg of the poly(arylene ether).
- the isolation of the mixture may be carried out in a devolatilizing extruder although other methods involving spray drying, wiped film evaporators, flake evaporators, flash vessels with metal pumps and combinations of two or more of the foregoing methods may be used.
- the isolated mixture may then be compacted, if necessary, by cold compaction or warm compaction as described above.
- Devolatilizing extruders and processes are known in the art and typically involve a twin- screw extruder equipped with multiple venting sections for solvent removal.
- the devolatilizing extruders most often contain screws with numerous types of elements adapted for such operations as simple feeding, devolatilization and liquid seal formation. These elements include forward-flighted screw elements designed for simple transport, and reverse-flighted screw and cylindrical elements to provide intensive mixing and/or create a seal.
- Particularly useful are counterrotating, non-intermeshing twin screw extruders, in which one screw is usually longer than the other to facilitate efficient flow through the die of the material being extruded.
- Such equipment is available from various manufacturers including Welding Engineers, Inc.
- the poly(arylene ether) powder may be compacted into small pellets, small disks with varying thickness or into large sheets of varying thickness.
- Useful compaction equipment includes both confined pressure devices and extrusion devices.
- a confined pressure device the poly(arylene ether) powder or powder mixture is directly consolidated in a closed mold or between two opposing surfaces. Compression is done either into mold to give a final shape or into a sheet or block that is later broken up to achieve the desired shape and size.
- extrusion devices the poly(arylene ether) powder or powder mixture undergoes shear and is consolidated while being subjected to pressure in a die.
- Extrudates may be formed under pressure in dies having a variety of cross sections and as they leave the die they may be broken up or cut to size.
- Useful confined pressure devices include pistons, molding presses, tableting presses, roll compactors, pre-getting rolls, briquetting rolls, gear pelleters and combinations of the foregoing. It should be noted that some compression rolls, while not individually comprising a cavity, nevertheless when used in combination with a second compression roll comprise a cavity between the two compression rolls.
- Extrusion devices include pellet mills, ring pellet mills, double roll extruders, and single screw and twin screw extruders.
- compression mold refers to the cavity in which the poly(arylene ether) powder is compressed, including a die head attached to an extruder.
- the pellets have a diameter of about 2 millimetres(mm) to about 25 mm, and a height of about 1 mm to about 50 mm.
- the disks have a thickness of about 1 mm to about 50 mm.
- the sheets have a thickness of about 2 mm to about 50 mm.
- the compression molding method may be used to prepare pellets having any arbitrary shape.
- Particularly useful pellet cross sectional shapes include spherical, cylindrical, cubical, elliptical right prism, ellipsoidal, cylindrical with torrispherical heads, elliptical with ellipsoidal heads, rectangular or square right prisms, rectangular or square right prism with rounded edges.
- the compression molding method is effective in manufacturing pellets having high bulk density compared to the poly(arylene ether) powder.
- the high bulk density of the compacted pellets reduces the volume occupied by the material during storage and transportation and thereby reduces the costs involved in the storage and transportation of the poly(arylene ether) pellets.
- the compacted poly(arylene ether) pellets may be fed to an extruder at higher feed rates than can be employed with poly(arylene ether) powder.
- the compression molded poly(arylene ether) articles may be subjected to further processing including sanding, and painting or powder coating and used in various, applications such as domestic electric appliances, electric and electronic parts, construction materials, automobile parts, communication devices and information management transmission parts.
- the molded material may be used in television housing, television chassis, deflection shock, other television parts, AC adaptor, electricity source box, air conditioner parts, audio parts, radiator cover, monitor housing, monitor chassis, liquid crystal projector housing, antenna cover, printer housing, printer chassis, scanner housing, scanner chassis, terminal adaptor, modem, and electric wiring insulation parts.
- bathtub parts shower head, pump housing, parts of air purifier, parts used in kitchens, pipes, gutter, sound barrier walls, window frame, toys, gardening tools, fishing tackles, foodstuff containers and cosmetic containers.
- Further automobile part examples include instrument panel, center console, meta console, glove box, airbag, defroster garnish, air duct, heater control, steering column cover, air defroster, door trim, sunshade, roof liner, pillar cover, pillar impact absorber, bonnet air scoop, radiator grill, signal lamp part, fog lamp part, door handle, door mirror, door panel, quarter panel, battery tray and battery housing.
- the compression molded poly(arylene ether) may find application in the aerospace industry. Applications include missile and aircraft stabilizer fins, wing ribs and panels, fuselage wall linings, overhead storage compartments, ducting, fasteners, engine housings and helicopter fairings.
- the compression molded sheets of poly(arylene ether) may find application in mines and thermal power stations due to their high impact strength and high abrasion resistance.
- Compression molded sheets of poly(arylene ether) may find application in the lining for the hopper of furnaces. In such applications the linings are frequently exposed directly to the fire.
- Ultra-high molecular weight polymers of poly(arylene ether) are excellent in chemical resistance and may give sheets having higher impact strength and abrasion resistance required for such critical applications.
- the raw material used in the following examples was a powder of poly(2,6-dimethyl-l,4- phenylene) ether having a density of 0.45 grams per cubic centimetre and an intrinsic viscosity of 0.41 dl/g as measured in chloroform at 25 °C and containing about 35 to about 45 volume percent particles with a size less than 100 micrometers.
- the compression mold consisted of a cavity in the form of a hollow stainless steel cylinder with a surrounding aluminum sleeve, with the cylinder measuring 55 mm in the outside diameter, 10 mm in the inside diameter or base diameter, and 45 mm in height. Also, the compression mold has a stainless steel piston, with the piston measuring 60 mm in height and 10 mm in diameter.
- Table 1 also shows the dimension ratio of the molded pellets which is a ratio of the diameter of the molded pellets in millimeter (mm) to the height of the molded pellets in mm.
- the compressive load as shown in the table is the load on the sample at the yield point. All the values shown in the table are an average of five tested samples.
- Example 2 The same procedure as in Example 1 was carried out, except that the mold consisted of a cylinder of 16 millimetres base diameter.
- the compression strength of the compression molded pellets in examples 7 to 9 is less than the compressive strength of the pellets in example 4 to 6.
- Example 4 The same procedure as in Examples 4-6 was carried out, except that the raw material used was a poly(arylene ether) powder with an intrinsic viscosity of 0.46 and containing about 35 to about 45 volume percent particles with a size less than 100 micrometers. 1.5 grams of poly(arylene ether) powder was filled in the compression mold at room temperature. The piston was then fixed, and a pressure was applied by a hydraulic compression for 5 seconds, after which the molded piece was taken out of the mold. These molded pellets were tested as in Examples 1-9. Results are shown in Table 4.
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- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/826,887 US7947204B2 (en) | 2004-04-16 | 2004-04-16 | Poly(arylene ether) compression molding |
PCT/US2005/011754 WO2005105921A1 (en) | 2004-04-16 | 2005-04-07 | Polyarylene ether compression molding |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1742998A1 true EP1742998A1 (en) | 2007-01-17 |
EP1742998B1 EP1742998B1 (en) | 2017-10-18 |
Family
ID=34965685
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05735268.4A Not-in-force EP1742998B1 (en) | 2004-04-16 | 2005-04-07 | Polyarylene ether compression molding |
Country Status (6)
Country | Link |
---|---|
US (2) | US7947204B2 (en) |
EP (1) | EP1742998B1 (en) |
JP (1) | JP2007532357A (en) |
KR (1) | KR100772745B1 (en) |
CN (2) | CN100551972C (en) |
WO (1) | WO2005105921A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7205342B2 (en) * | 2003-10-10 | 2007-04-17 | General Electric Company | Poly(arylene ether) composition and method of molding |
US7947204B2 (en) * | 2004-04-16 | 2011-05-24 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether) compression molding |
US20060038324A1 (en) * | 2004-08-20 | 2006-02-23 | Yeager Gary W | Molding method for curable poly(arylene ether) composition and article thereby |
EP2169007B1 (en) | 2008-09-30 | 2012-07-11 | SABIC Innovative Plastics IP B.V. | Method for preparing a poly(arylene ether) composition with improved melt flow |
US8017716B2 (en) | 2009-07-01 | 2011-09-13 | Sabic Innovative Plastics Ip B.V. | Morpholine-substituted poly(arylene ether) and method for the preparation thereof |
US9745693B2 (en) | 2014-03-18 | 2017-08-29 | Schroth Safety Products, Llc | Flame resistant fabric for aviation airbags |
EP3463791A1 (en) * | 2016-05-24 | 2019-04-10 | SABIC Global Technologies B.V. | Poly(phenylene ether) molding method and articles, and method of increasing poly(phenylene ether) crystallinity |
JP6581064B2 (en) | 2016-10-28 | 2019-09-25 | 旭化成株式会社 | Polyphenylene ether powder and production method |
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US3078254A (en) * | 1959-07-20 | 1963-02-19 | Phillips Petroleum Co | High molecular polymers and method for their preparation |
BE627652A (en) * | 1962-01-29 | |||
US3297793A (en) * | 1962-12-21 | 1967-01-10 | Phillips Petroleum Co | Continuous process for producing block copolymers of dienes and vinyl aromatic compounds |
US3402159A (en) * | 1963-12-20 | 1968-09-17 | Phillips Petroleum Co | Process for polymerizing butadiene and styrene terminated in short blocks of polystyrene |
US3408437A (en) * | 1966-07-20 | 1968-10-29 | Union Carbide Corp | Molding thermoplastic printing plates |
US3356761A (en) * | 1967-04-12 | 1967-12-05 | Gen Electric | Melt processable polyphenylene ether and process |
JPS5125394B1 (en) * | 1967-09-30 | 1976-07-30 | ||
US3594452A (en) * | 1968-02-06 | 1971-07-20 | Shell Oil Co | Polymers prepared from monolithiumterminated block copolymers and certain diesters |
BE747591A (en) | 1969-04-01 | 1970-09-21 | Shell Int Research | BLOKCOPOLYMEREN MET EINDSTANDIGE STATISTISCHE COPOLYMEERBLOKKENVAN STYREEN EN ALFA-METHYLSTYREEN |
US4154775A (en) * | 1977-09-06 | 1979-05-15 | General Electric Company | Flame retardant composition of polyphenylene ether, styrene resin and cyclic phosphate |
GB2043083A (en) | 1979-03-06 | 1980-10-01 | Gen Electric | Flame retardant polyphenylene ether compositions |
US4434118A (en) * | 1980-12-23 | 1984-02-28 | Stauffer Chemical Company | Compacting polycarbonate and copoly(carbonate/phosphonate) particles |
DE3203186A1 (en) * | 1982-01-30 | 1983-08-11 | Röhm GmbH, 6100 Darmstadt | POLYARYLENE ETHERS CONTAINING PHOSPHORUS |
NL8502116A (en) * | 1985-07-24 | 1987-02-16 | Gen Electric | PROCESS FOR PREPARING A POLYMER MIXTURE CONTAINING A POLYPHENYLENE ETHER AND A POLYAMIDE |
US5019311A (en) * | 1989-02-23 | 1991-05-28 | Koslow Technologies Corporation | Process for the production of materials characterized by a continuous web matrix or force point bonding |
JP3109175B2 (en) * | 1991-09-26 | 2000-11-13 | ジェイエスアール株式会社 | Method for producing crosslinked polymer |
DE4140499A1 (en) | 1991-12-09 | 1993-06-17 | Danubia Petrochem Deutschland | Composites contg. polyarylene ether-ketone and/or polyphenylene sulphide and/or thermoplastic polyester - formed by press-moulding the components together at a temp. between the Tg and the m.pt. of the polymer |
DE4142578A1 (en) * | 1991-12-21 | 1993-06-24 | Basf Ag | METHOD FOR PRODUCING THERMOPLASTIC MOLDING MATERIALS BASED ON POWDER-SHAPED POLYPHENYLENE ETHERS AND VINYLAROMATIC POLYMERS |
DE4328873A1 (en) | 1993-08-27 | 1995-03-02 | Basf Ag | Polyarylene ether agglomerates |
US6194518B1 (en) * | 1996-11-01 | 2001-02-27 | General Electric Company | Solid polymer dispersions and method for their preparation |
US5767426A (en) * | 1997-03-14 | 1998-06-16 | Hoeganaes Corp. | Ferromagnetic powder compositions formulated with thermoplastic materials and fluoric resins and compacted articles made from the same |
US6359043B1 (en) * | 1998-09-24 | 2002-03-19 | General Electric Company | Mica as flame retardant in glass filled noryl |
JP2000167827A (en) | 1998-12-03 | 2000-06-20 | Asahi Chem Ind Co Ltd | Manufacture of polyphenylene ether tablet |
JP4152521B2 (en) * | 1999-04-16 | 2008-09-17 | 旭化成ケミカルズ株式会社 | Production method of polyphenylene ether powder with improved particle size distribution |
US6534564B2 (en) * | 2000-05-31 | 2003-03-18 | Hoeganaes Corporation | Method of making metal-based compacted components and metal-based powder compositions suitable for cold compaction |
US6617295B2 (en) * | 2001-04-27 | 2003-09-09 | Polyone Corporation | Composition and method for foaming resin |
EP1389514B2 (en) | 2001-05-24 | 2015-11-04 | Toray Industries, Inc. | Tablet, process for producing the same, and molded article obtained therefrom |
US7947204B2 (en) * | 2004-04-16 | 2011-05-24 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether) compression molding |
-
2004
- 2004-04-16 US US10/826,887 patent/US7947204B2/en active Active
-
2005
- 2005-04-07 JP JP2007508395A patent/JP2007532357A/en not_active Withdrawn
- 2005-04-07 EP EP05735268.4A patent/EP1742998B1/en not_active Not-in-force
- 2005-04-07 CN CNB2005800149725A patent/CN100551972C/en not_active Expired - Fee Related
- 2005-04-07 WO PCT/US2005/011754 patent/WO2005105921A1/en active Application Filing
- 2005-04-07 CN CN200910204908.3A patent/CN101670638B/en not_active Expired - Fee Related
- 2005-04-07 KR KR1020067021320A patent/KR100772745B1/en active IP Right Grant
-
2011
- 2011-04-28 US US13/096,432 patent/US8703028B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO2005105921A1 * |
Also Published As
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US20110198773A1 (en) | 2011-08-18 |
CN101670638A (en) | 2010-03-17 |
KR20070004038A (en) | 2007-01-05 |
KR100772745B1 (en) | 2007-11-01 |
JP2007532357A (en) | 2007-11-15 |
CN100551972C (en) | 2009-10-21 |
CN1950452A (en) | 2007-04-18 |
US7947204B2 (en) | 2011-05-24 |
WO2005105921A1 (en) | 2005-11-10 |
US8703028B2 (en) | 2014-04-22 |
CN101670638B (en) | 2014-08-13 |
EP1742998B1 (en) | 2017-10-18 |
US20050230869A1 (en) | 2005-10-20 |
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